Watch: 27 Times Alison Krauss Made GRAMMY History

Relieve Alison Krauss' unprecendented GRAMMY history from her first win for Best Bluegrass Recording for "I've Got That Old Feeling" for 1990 to her work with Union Station and her Best Bluegrass Album-winning Paper Airplane.

From her first win for Best Bluegrass Recording for "I've Got That Old Feeling" for 1990 to her work with Union Station and her Best Bluegrass Album-winning Paper Airplane, Alison Krauss has made history with 27 GRAMMY wins throughout her career, the most GRAMMYs earned by a woman.

Relive her unprecedented run with this look back at the country/folk singer/songwriter's GRAMMY highlights, including her performance with Robert Plant and producer T Bone Burnett at the 51st GRAMMY Awards in 2009.

Learn more: Who are the top GRAMMY winners of all time?

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